I Guess I'll See You Around
by starrily-night
Summary: Dean Winchester wakes up after a car accident and meets his roommate, Castiel Milton. What happens afterwards will baffle Sam for years to come. AU, eventual Destiel, possible Sabriel. Based off a photoset from Tumblr.
1. An Awkward Phone Call

**This is based off a photoset someone made on Tumblr in which Dean and Cas were both in hospital wear and there was a whle tag talking about this idea and I said "FUCK YEAH, I'M WRITING THIS." So here it is.**

**starrilynight(.)tumblr(.)com/post/13697490598/bestillmyshippingheart-castielismycopilot is the link to the post.**

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><p>The first thing Dean Winchester hears when he wakes up is, "Gabriel. Please, please stop sending all these prostitutes to my room. No, I don't care if you think I need them, I am physically incapable of having sex right now."<p>

He opens his eyes groggily. He can't remember much and the room is spinning like he's drunk even though he isn't. The smell is too clean, the feel is too scratchy, and the look is too white.

Then he remembers smashing metal, someone screaming, and his little brother doubled over in the backseat of the crashed car, his dad's eyes wide open and glassy, and he sits bolt upright, gasping and clutching at his chest.

"Oh, hold on. My roommate just woke up." There's a click and Dean turns to see who else is in the room with him.

In the bed next to his is a guy with a shock of unruly dark hair and bright blue eyes that Dean finds strangely irresistible. He's staring at Dean with a look of curiosity on his face. Probably mirroring the one on Dean's face.

"Morning, Sleeping Beauty." The man sounds slightly amused. Dean groans as he collapses backwards.

It's silent for a long moment and the Dean says, "How long have I been here?"

"Three days." Castiel's voice sound muffled, like he has something in his mouth. "Want a lollipop? My brother keeps bringing them for me- too many for me to eat."

Dean sits up and reaches up a hand to catch the red sucker the other man throws across the room. "Thanks. Who are you, anyway?"

"My name is Castiel." the man says, pulling the lollipop out of his mouth. "Castiel Milton. And yours?"

"Dean Winchester." Dean grunts as he sits up, unwrapping the lollipop and putting it in his mouth. "Castiel, huh? Cool name."

"It's from the Bible." Castiel looks a little sheepish. "My family is very religious. My brother is Gabriel. My cousins, Michael and Lucifer." Dean shivers slightly at the name of the Devil. Castiel notices. "No, neither of them are particularly evil. Neither of them like me very much but… it is unavoidable." He shrugs. "What about you?"

"My family?" Dean chuckles. "My little brother, Sam. He's the only family I have left, after…" He stops as he realizes what must've happened in the crash.

"My dad." He realizes, just as the nurse walks in. She's pretty, with red hair and good-sized boobs, but Dean barely takes notice of her until she's at his side.

"Good to see you awake, Mr. Winchester." She's cheery, her smile pretty. Dean flashes her a grin and she reddens slightly. "Now, your vitals seem to be all right-"

"Where's my little brother?" Dean interrupts. He doesn't really care about himself right now. Across the room Castiel quirks him a half smile.

The nurse looks shocked for a moment and then her expression clears. "Oh, Sam? He's in Kansas right now. He's all right."

"Kansas? Why-" It hits Dean like a train at that moment- his father's gone.

"It was your father's last wish to be buried with your mother. Sam went with his body to make sure it happened. We can contact him, tell him you're awake, unfortunately he didn't leave us a number…"

Dean knows this. He spots a piece of paper and a pen on the table next to his bed and grabs it, writing down a number. "What happened to Sam? He's okay, right? Last I saw he was doubled over in the backseat of my car…"

"He suffered several long scratches and was in shock when we found him, but was otherwise all right. You, on the other hand, suffered a head injury that could've caused brain damage. Luckily for you it didn't. You also cracked a bone in your ankle and had a dislocated shoulder- we're going to have to keep you under observation for three weeks."

"Three weeks?"

"Sorry, but you wouldn't be able to do much if we released you now." The nurse gave him a sad sort of smile and then turned to his roommate. "Ah, I see Gabriel brought you some more lollipops. That's nice, isn't it?" The jar by Castiel's bed had to be full of a good two hundred lollipops.

Castiel gave a grunt and a noncommittal jerk of his head. Dean had a sudden idea.

"Hey, are the kids down in the cancer wards allowed to have candy?"

The nurse turned. "Uh, yes, why?"

"I don't think either of us are gonna be able to eat that many lollipops, so maybe you could bring them down for the kids…"

"That's a BRILLIANT idea!" The nurse beamed and glanced at Castiel, who nodded, holding out the jar to her. Beaming, the nurse exited the room.

Castiel turned to face Dean and grinned. "Dean Winchester, I think this is going to be the start of a beautiful friendship." he proclaimed.

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><p><strong>Oh, blimey. Just leave a review I guess? PLEASE?<strong>


	2. Gabe gets pissed and Sam is relieved

**So basically Cas in this story has a 2014!Castiel personality, because it's more fun to write him that way. SORRY FOR THE SLOW UPDATE. I PROMISE TO THINK AHEAD BETTER WITH THIS STORY.**

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><p>Dean was beginning to enjoy his time with Castiel. The two had a lot to talk about- estranged fathers, mothers long gone, and most importantly, their families.<p>

"What's your brother like?" Castiel asked.

"He's a fucking genius, man." Dean laughed. "He's in his last year of college, hopefully going to law school. I mean, if he can get a full ride. If he can't he has to drop out, because at this point we have no money left."

Castiel was silent, staring out the window in the hospital room, although he looked contemplative.

"Shit, I'm tired." Dean yawned. "What time is it, anyway?"

"Nine thirty."

"Whoa. I'm never asleep this early." Dean chuckled and rolled over. "Anyway. 'Night, Cas."

He missed Castiel's strange look at the nickname.

He was woken up several times for vital checks, but apart from that, he slept a good sixteen hours. When he woke up again, Castiel was grinning.

"Gabe was slightly pissed you were still asleep." The other man chuckled.

"So when is he going to be visiting again?" Dean asked him. "You know, so I make sure I'm not asleep."

"He left here about ten minutes before you woke up, so he'll be back tomorrow." Castiel chuckled. "Unless he discovers that I stole his phone. Which I did."

Dean grinned. "How long do you think it'll take for him to realize-" he began, and was interrupted by a loud yell from outside.

"CAS!"

"Damn." Castiel's eyes were alight with mischief. "I thought he'd at least be halfway across the state by now."

Dean laughed, just as the door to their hospital room slammed open.

Dean carefully gazed at the man in the doorway and finally, he managed, "Dude… you're short."

"Bite me." Gabriel snapped. "Cas, my phone. Now."

"Fine." Castiel handed over a battered black phone which he seemed to produce from nowhere. "Honestly, Gabe, you're no fun."

"I seriously needed to make a call an hour ago, Cas." Gabriel fumed. "Now Zach's gonna be pissed at me and you know how bad that gets."

"At least you can't blame me." Castiel responded cheerfully. "He'll say it was because you weren't paying attention."

"Zach?" Dean asked, furrowing his eyebrows.

"My older brother." Castiel explained quickly. "And Gabriel's boss."

"Well!" Gabriel seemed to suddenly notice Dean was awake. "Look who crawled out of the coma-cave."

"What the he- Gabe, that's not a real saying!" Castiel was trying to suppress his mirth as he glared at his brother.

"I know." Gabriel smirked. "I just made it up."

"So you're Gabriel." Dean looked up at the short man. "You're a bit smaller than I expected. What happened- did you get flattened one too many times in Mario Kart or something?"

Gabriel paused, looking slightly shocked, and then laughed. "I like him." he told Castiel. "He's snarky."

"Stick around and I'll show you just how snarky I can be." Dean informed him.

"Sadly, I can't." Gabriel stuck out his lower lip. "I have to leave you two to your flirting."

"Flirting?" Castiel and Dean questioned as one. Gabriel laughed and sauntered out of the room.

"I'm going to kill him." Dean said, leaning back against his pillow.

"Most people say that." Castiel said, popping another lollipop in his mouth. "But once you get to know him, he's really not a bad person."

The nurse from before reentered the room, portable phone in hand. "Mr. Winchester, your brother finally picked up his phone. He's waiting."

"Awesome." Dean took the phone from her. "And you can call me Dean."

The nurse blushed. "Anna." She said, exiting the room quickly. Castiel whistled.

"You got a name out of her. Better than I could do." He chuckled.

"It's the smile. Wins the ladies every time." Dean put the phone to his ear. "Sammy?"

He had to pull the phone away. "Sam! Sam, calm the hell down."

"Sorry, Dean." Sam apologized. "I just haven't heard your voice in three days. I was worried. Are you okay?"

"I'm fine." Dean replied. "Just cracked a bone in my ankle or something- they're keeping me here for another three weeks to make sure I don't die or something."

"Oh." It was silent on the other end for a moment. "I'm still in Kansas. Sarah met me here- we'll come by in a couple days."

"Right." Dean remembered something. "You know my roommate?"

"Uh… that Castiel dude, right?"

"Yeah. Just a warning- his brother's a bit of a bastard."

"How big is he?"

"He's a fucking _elf._"

"I think I'll be okay."

"See you in a couple of days then?"

"Yeah." A pause. "Sarah says hi."

"Hi Sarah." Part of Dean wishes Sam would just man up and ask Sarah out already. The two are perfect for each other and Sam needs someone like her after losing his fiancé in a freak house fire two years before.

"Bye Dean."

"See you later, Sammy."

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><p><strong>Aaaaaaaand you know the drill! Review, fave, follow! Love you all!<strong>


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